The city bike got a flat on the way to a pitch and run.
I had left exactly no margin for that.
The plan was to meet an investor in person and run together. This is a nearly perfect meeting format for me. It gets everybody out of a conference room, keeps the conversation moving, and removes the question of what to do with your hands while explaining a company that barely exists.
Instead, I was late enough that the run did not happen.
I sent the apology that evening. I had gone out that morning for the pitch and run, the bike went flat, and I had not built in enough buffer to recover. I still wanted to meet. I just had to admit that the guy pitching an organizational product had failed at organizing the trip across town.
Loop was still very early. I had left Pinata to build it with Caroline, and we were trying to raise money while the first version of the product was still under construction.
That creates a specific kind of fundraising conversation. You are not showing somebody a finished thing and asking whether they like it. You are asking them to believe that you understand the problem, that the team can build the answer, and that the answer will matter once it exists.
The gap between the story and the product was uncomfortable because it was real.
A couple days later, after another investor response, I told Caroline not to let it disappoint her too much. We had worked with a part-time designer for five weeks. We were asking people to take a big bet. Plenty of investors were going to want a very specific kind of proof before they could get there.
That did not mean the response felt good. It meant the response made sense.
The Alpha was not ready for outside testing yet. I told another investor that we were making progress every day and expected the first version in a few weeks. He would be one of the first people we invited when it was ready.
That was the honest version of the pitch. There was no fake waitlist momentum or polished product theater. There was a product being built, a team asking for capital, and a long list of people we hoped would try it as soon as they actually could.
The missed run stayed with me because it compressed the whole period into one morning.
I was building a networking company, trying to meet investors through the network, using a run to make the meeting more human, and relying on an old city bike to get there. Then the tire went flat.
The skyline still looked excellent from Brooklyn.
I fixed the next meeting. We kept building the Alpha. I probably should have left fifteen more minutes.